Azo derivatives and their use in dyeing



Patented Sept. 17, 1935 l i I 2,014,423

UNITED STATES PATENT orries I 12.0mm I szo nmvsnvns sun rum use at nrsmaDavid -Alexander ,Whyte Fairweather and Robert Fraser Thomson,Grangemouth, Scotland No Drawing. Application June 9, 1932, Serial No.mass. [n.Great Britain Jane 19, 1931 I 'IClaims. (cu-s) This inventionrelates to an improved dye and although other solubilizing groups mightalso be more particularly refers to an azo dye having used withexcellent results. Upon the addition. superior characteristics andmethods for its proof'a diazo solution to a neutral oracidic solutionduction. V I e of the 2-3-hydroxy-naphthoic arylide described *6 It isan object of this. invention to produce an above,- coupling takes place.Where the starting I I am derivative which may be applied to the fibermaterial is i-sulfo-z-il-hydroswnaphthoic arylaud thereupon renderedinsoluble by suitable ide, coupling will occur in the one position.treatment. A further object is to produce an If the diazo solution isthen cautiously treated insoluble azo dye. Additional objects willappear with an alkali, preferably sodium carbonate, it 10 hereinafter. yis converted to anaphthoquinone. The naphthol These objects areaccomplished by the present quinone is readily changed to the coinvention wherein a 2-3-hydromaphthoic arylazo. compound by treatmentwith an acid; sulide, having substituted thereon a solubilizing furicacid having been found to give excellent swap. is coupled with a diazocompound. This results. This acid treatment splits oi! the solulscompound maybe converted to a naphthoquinone bilizing group and rendersthe compound insolu- II by cautious treatment with alkali. The naphble.By treating the material to be dyed with hoquinone may then readily beconverted to the the compound before splitting oi! thesolubiiizcorresponding azo, derivative by treatment with I ing group a eis obtained which is exceptionally an acid. fast to w g. 7 so Theinvention may be more fully understood The process of the presentinvention is not so by reference to the following examples: I confinedto the case where the material to be hump,'dyedistreatedsolelywiththeproductsmentioned herein, since it is alsointended to cover treat- 1 10.8 parts of fi-nitro-ortho-aminoanisolewere ment of the material with other products, such as g diasotisedin'theusual mannerandthe diazoenolicsulfuricesterssltsofvatdyestuifsorothergs solution neutralizedwith sodium acetate. To quinones, including such enolic sulfuric esterthis solution was added,while stirring a solution salts. as areconverted to dyestufls by the action of 36.6 parts ofsodium-2:3-hydroxynaphthoicof acid alone orwhere they are treated withdyes anilide-l-sulfonate. The red precipitate was 111- corresponding toBritish specification No. 333,508,

39 tered or and washedwlth in conjunction with the compounds of thepres- N' The cake was suspended in water, containing ent invention.Excellent results maybe obtained 10 parts of sodium carbonate, atordinary. temby using the compounds of the present invention perature,for a few minutes, and the dyestuif was in conjunction with other dyesand this comfilteredoflandwashedwith-brine;bineduse-isintendedtobecoveredbythepres- 5 r ent invention. II

' v 1 v Y As many apparently widely different embodi- A dye bath wasmade up by adding to 4000 ments of this invention may be. made withoutparts ofwater, 6 parts of a 10% paste of the dyedeparting from thespirit and scope thereof, it stuflobtainedbythemethodofltxample 1.lstobeunderstoodthatwe donotlimit ourselves At 40-50 100 parts of woolwere entered and to the specific embodimentsthereof except as de- 0 Ithe temperature was gradually raised to 90 while 'fined in the appendedclaims. working the material, Exhaustion was eifected vWe claim: v bythe addition of small quantities of acetic acid. 1. A process whichcomprises reacting a 2-3 When exhaustion was complete, 10-20 parts ofhydroxy-naphthoic arylamide, having substituted sulfuric acid were addedto the bath. After a thereon in the one-position a solubillaing group, I

few minutes the formation of the insoluble azo with a diazo compound,-treating the resulting dyestui! was complete and the wool was lifted,compound with an alkali, impregnating the fibers washedand finished. tobe dyed with the productthereof, and fixing It is to be understood thatnumerous 2-3- thedye thereon by treatment with an-acid. sohydroxy-naphthoic arylides may be used as start- 2. A process whichcomprises reacting a l-sulfol0 ing materials in carrying out the processof the 2-3-hydroxy-nap thoic arylamide with a diaso present invention.These compounds should compound, treating the resulting compound withcontain a' solubilizing group. which renders them an alkali,impregnating the fibers to be dyed with readily soluble'in water. Thesulfonic acid group I the product thereof, and fixing the dye thereonbyv has been found to give very satisfactory results, treatment with anacid. a I

3. A process which comprises reacting a. l-sulfo-2-3-hydroxy-naphthoicarylamide with a diazo compound, treating the resulting compound withsodium carbonate, impregnating the fibers to be dyed with the productthereof, and fixing the dyethereon by treatment with an acid.

4. The process of claim 3 wherein the dye is fixed on the fiber bytreatment with sulfuric acid.

5. A process which comprises reacting diazo-' tized5-nitro-o-aminoaniso1e with 1.-sulfo-2-3- hydroxy-naphthoic-anilide,treating the resulting compound with sodium carbonate, impregnating thefibers to be dyed with the product thereof, and

fixing the dye thereon by treatment with sulfuric acid.

6. A process for producing insoluble azo dyes which comprises treating acompound having the following general formula:

O ONE-Bi o ON -R,

wherein R and R1 represent the residues of arcmatic amines of thebenzene series, free from water'-so1ubilizing groups, with sodiumcarbonate, impregnating the fibers to be dyed with the product thereof,and fixing the dye thereon by treatment with sulfuric acid.

DAVID A. W. FAIR-WEATHER. ROBERT; FRASER THOMSON.

